Hydrochloric Acid → HCID 66939110, compound

HRID 1257435Notes

Reaction equation

HRID 1257435 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)=[CH:5][C:6]=1[CH2:7][N:8]1[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[CH:10]=[N:9]1.[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[O:3][C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=2)=[CH:5][C:6]=1[CH2:7][N:8]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[N:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66939147HCID 66939147, compound

Product 1

HCID 66939110HCID 66939110, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (0.35 g) obtained in Example 127c was dissolved in ethanol (3 mL), and 6N aqueous sodium hydroxide solution (0.77 mL) was added. The reaction mixture was heated under reflux for 2 hr, cooled in an ice bath, adjusted to pH 2 with 6N hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate, concentrated under reduced pressure, and the residue was purified by column chromatography (carrier: silica gel, eluent: dichloromethane/methanol) to give the title compound (0.25 g) as a colorless solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hr
  3. temperaturecooled in an ice bath
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by column chromatography (carrier: silica gel, eluent: dichloromethane/methanol)

Sources & evidence

ORD record
ord-9f8866a58fdf4746ad86864535331f38
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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